Unexpected Places the Heart Leads Us
by blueyed18
Summary: Rory had the best of both worlds, and she had everything a girl could ask for. Her world is in for a huge surprise.
1. Meet the Chilton Queen

Disclaimer: I do not own anything related to Gilmore Girls. Sadly, the only thing I own is my original characters and plot.

A/N: Hey guys! Umm, story. I know I know, I need to update my others especially Arranged Marriage. Alas, in posting this story I have reawoken the muse within my self and I should have updates on all of my other stories soon. I promise. So, this chapter is a little prologue basically. I have fallen in love lately with stories where Rory and Logan grew up together as best friends so I decided to take a stab at it myself. I haven't really tried to write angst before so here it is. Although the first chapter is angst free it'll come shortly after. Hope you enjoy!

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Rory had a great life. She honestly did, but she's always felt like something was missing. She has a great family, the best friends a girl could ask for, and she was finally a senior in high school.

She had gotten up extra early this morning, it was the first day of school and Rory was having a hard time sleeping anyways. Damn that Finn calling her at 5 a.m. to let her know what today was like she didn't know. She is Rory Gilmore-Hayden, ruler of all bookworms.

Rory knew the real reason why Finn called this morning. He needed a ride. See, that's the thing with Finn. Leave it to him to be drunk at 5 a.m. the day before school starts. He called Rory because he knew she'd show up the next morning and drag his hung over ass out of bed. She is the most reasonable one of the group. She's got the eyes that will make any boy or man do anything that she asks. This makes her a girl with great power in the Chilton halls. Being the best friend of the three most eligible bachelors in Hartford comes with a power in itself.

Girls generally either love her or hate her. Honestly, she was okay with that. Especially the latter, she hated when girls tried to be her friend just to get to the boys. Call her overprotective, but she just hated girls whose only aspiration was to be a Hartford trophy wife. Her boys deserved better than that.

Rory put the finishing touches on her appearance and grabbed her backpack. She had pulled her loose curls in a pony tail so she could leave the top down in her red mustang convertible. Rory really did have the best of both worlds. She had the perks of her high society life, but she had the personality of the small town girl whom everyone loved. She loved a good book and a great party at the same time. She felt really well balanced. She seemed like the perfect person, at least to outsiders and she liked it that way. Only those close to her knew the real Rory and she felt a lot safer that way. She finally had made her way to Finn's house to start her day as the senior Chilton queen.

XXX

Rory pulled up to the Morgan estate. 'Deathly quiet as usual,' she mused. She made the walk up to Finn's door and let herself in. Rory didn't bother to knock, she knew Finn hated the wait staff. He almost always told them to go home when his parents weren't home which was almost always. Rory opened up the door to Finn's room and peeked inside, messy as usual.

"Finn get your exotic ass out of bed! You know I hate being late for the first day of school."

"Mmph. Go away love."

"Finnegan Morgan! I mean business mister. Do NOT make me get Gellar over here!"

"Now Rory, why would you tease a man like that? It's not nice."

"Man? I don't see a man in here. Last I knew, a grown man could get himself out of bed on time with out the help of his best friend."

"Love, trust me. I am a grown man," he wiggled his eyebrows to make his point.

"Ten minutes or I get Gellar!" Rory threw his Chilton uniform on the bed and headed downstairs for another cup of coffee while she waited. She had a feeling she was going to need it.

XXX

Twenty minutes and a phone call to Paris later, Rory was finally standing in front of her locker. She smiled to herself remembering Finn practically catapult himself out of bed this morning. It was always interesting when Paris and him are together. She dropped a book as someone's hands covered her eyes.

"Good morning beautiful."

"Huntz, I smell coffee. Gimme!"

"Now Ace, not even a hello Logan? How are you? I mean I haven't seen you in weeks! Even you have a hard time staying away from me that long."

Rory turned around and threw her arms around Logan. "I'm going to ignore that comment until later."

"I honestly did miss you Rory. Fiji was lonely without you."

"Just because you didn't have me there to get you out of trouble. At least Finn wasn't with you this year so I know you behaved at least the slightest bit." Rory beamed up at him. Out of all her friends Logan knew her the best. After all, they've known each other since they were three. If she was completely honest with herself she knew she had missed him the last two weeks. Sure they talked on the phone almost everyday but it wasn't the same.

"Awe, Ace. You know me too well." Logan smiled down at his best friend and tightened his grip around her.

"Look here Colin. Our lovely mate has returned from beyond! Are we speaking to him?" Finn had been a little bitter when Logan announced to the gang that he was going on vacation alone this year.

"I don't know Finn, I'm just a tight ass remember?"

Logan flinched at the memory. His friends hadn't been very happy with Logan and that upset him. "Look guys, I thought we already talked about this..."

Colin and Finn just smiled at each other before tackling him in the hallway. "It's good to have you back mate!"

Logan looked around at his best friends and smiled. 'It's great to be back,' he thought.

Rory smiled at the three stooges. Yes, this year was going to be great. Nothing could change that. If she had only known then what was in store for the rest of the year, she might've thought differently.


	2. Why hello there!

Disclaimer: Sadly, I own nothing like always.

So I'm happy to report a fairly good timed update! It's a record for me, but I'm just so excited about this story. I loved all the reviews I got! Thank you all so much! I could always use some more though. wink wink If you haven't, you should check out my story Arranged Marriage, it's actually been updated tonight as well. Anyways, enough of that. On with the chapter! It's unbeta'd so I'm terribly sorry if it sucks!

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Rory walked away from the boys to find Stephanie and Rosemary. It's not that she didn't love the boys, she just sometimes needed some female company. The boys weren't exactly the greatest people to have around for shopping trips, Rory learnt that the hard way. Rory and Steph met in the 5th grade when Stephanie transferred to Hartford from somewhere in California. Her parents were from old money just like the rest of the gang. Stephanie's grandparents had died in a tragic car accident making their heir, Steph's dad, take over the family business. This being the case, the group got to know Steph over time and by the time the 6th grade started the girls were pretty inseparable.

They met Rosemary by pure chance their 1st year at Chilton. Finn had started out looking for his first conquest stating he couldn't be a virgin in high school, it just wouldn't do. He thought Rosemary would be a great place to start but boy was he wrong. Ever since then he has been obsessed with all girls of the red headed persuasion. Rory and Steph took to her instantly for putting their crazy Aussie friend in his place. Of course they loved the fact that they were no longer outnumbered by the boys even more.

Rory smiled to herself thinking of how much has changed throughout high school. She turned the corner to see the girls looking in their mirrors that they had strategically placed inside their lockers. Well, some things haven't changed. Just as Rory was going to say hi someone knocked into her causing her books to fly everywhere. Her oh so precious books! "Would you please watch where you're..." Rory lost all train of thought because she was captivated by a very green pair of eyes.

"I am so sorry. I'm new here and got lost somewhere along the way. I really am terribly sorry for running into you the way I did. Let me help you with your books."

Rory watched as the very tall mystery man picked up all of her books and then turned towards her giving her a stunning smile that made her insides melt.

"Here you go. My name is Landon. I know we didn't get off on the right foot, but I was wondering if you could point me in the right direction of where Mr. Halls government class is?"

"Um...it's right down that hall." Rory could barely get the words out of her mouth. He was beautiful with his black hair, tall, green eyes, tan, he was almost like a Greek god.

"Thank you so much. I'm sorry again for running into you...I don't believe I got your name?"

"R-Rory."

"Well, Rory. It was a pleasure meeting you."

He sent Rory a wink as he turned down the direction she pointed earlier. She couldn't believe it. For the first time in a long time she was speechless in front of a boy. A very handsome boy at that.

"Oh my god Rory! Who was that yummy eye candy?!" Stephanie squealed as she shut her locker.

"He said his name was Landon, new kid." Leave it to Steph to be the first to ask. She was pretty boy crazy.

"Lucky you Ror, I saw him earlier today trying to get away from all the Chilton sluts. They were all trying to get his attention but he just wasn't buying. I'm jealous I wasn't the one he asked how to get to his class!"

Rory looked at Rosemary's pouting face and laughed. "Don't worry Rose, I'm not interested. He's all yours." _Yeah right Hayden. You know you're interested._

"Rory, never in the three years that I've known you have I seen you get speechless in front of a boy!"

"Shut up! That doesn't mean anything at all and you know it. Steph, you believe me right?"

"Yeah, sure. I believe that a gorgeous boy flirted with you, which left you speechless, and that you are not interested at all. Right."

"Ugh! Why I wanted to come see you guys instead of staying with the boys I do not know." Rory rolled her eyes as she headed towards home room, all the while thinking about the green eyed stranger she met moments before.

XXX

Rory made it through the first half of school with barely any homework; however, that didn't mean she wasn't any less ready for lunch. She was starving and she missed her friends, especially Logan. She didn't have any classes with him in the morning which was unusual for them. Being best friends with powerful last names got them a lot of classes together. Rory didn't like the fact that she only had 2 classes with him this semester: English and Chemistry. She couldn't forget that he would be on the Franklin with her. She couldn't face Paris alone.

"Gilmore-Hayden!" Rory groaned at the sound of the she devil's voice. Did she mention that she was really ready for lunch?

XXX

Logan couldn't believe it was finally his senior year. This time next year he would be settling in his dorm room at Yale starting his search for the luckiest girl to be his first college conquest. Logan sighed, he really loved his life.

Logan glanced towards the cafeteria doors to see Rory, his best friend, walk in with their lovely editor Paris trailing behind her shouting something.

"I expect you to be at the Franklin on time this year Rory. It's imperative that we set an example for the incoming members!"

"Paris, have I ever been late to a meeting?"

"Well, no-"

"Exactly, now leave me the hell alone! I'm hungry." Rory huffed as she walked away from Paris. As she sat down she heard Logan chuckle. "Something funny there Huntzberger?"

"Nope not at all, Ace. Just laughing at how I know you're hungry that's all."

"Well duh, I said I was."

"Anybody could see that Ror, I know you're hungry without you having to say it. Comes with the title of being the best friend."

"Okay oh great one, enlighten me."

"You get really feisty when you're hungry, I like it."

"Ugh, you're such a pig!" Rory slapped him on his chest, but Logan caught her hand.

"But you love this pig. Admit it Ace, you'd be lost without me."

Rory looked at a smirking Logan and couldn't help but smile. She really did love her best friend. He always had a way of making her laugh, even when she thought she couldn't. "Whatever Huntz, I don't need to give you a bigger head."

"Dirty." Rory looked up to see Finn sitting down at the table. Next thing she knew Logan was dropping her hand and she surprised herself by being a little disappointed. "Finny dear, quit being a pervert. You know I save those kind of comments for you and only you."

"Rory love, oh how you tease me. When will you realize that you are madly in love with me? Then we can finally run away to Australia like I've been fantasizing about."

"Maybe when Logan here settles down on one girl I'll think about."

"What about it mate? Give an Aussie a chance here."

"Sorry man, no can do. It's just not in the DNA."

Rory laughed at two of her great friends as they continued their banter. Her mood changed completely as a certain green eyed boy threw yet another wink her way as he headed to get his lunch.

"Who was that Ace?"

"Yeah, love. Seems like someone has an admirer."

"He's nobody Finn. Just a boy that bumped into me earlier by accident."

"Yeah, accident. I've used that technique a hundred times."

"Finn's right Ace. Wow, that was a surreal moment."

"You two are overreacting. Don't worry about it. He's just a new friend, that's all." Rory turned and looked at Landon as she finished her sentence. Right, a friend was all he could be.

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I'd love you forever if you clicked that little purple button at the bottom and tell me how I'm doing! It encourages me to keep on writing. 


	3. Overprotective

Chapter Three – Overprotective

So the Christmas holidays were completely crazy. Then I became obsessed with catching up on reading some fanfic. Alas, here's another installment. And yes, this will eventually be a Rogan. No fears, they're just going to have to go through a lot to get together. It won't be easy. Hope you like it! Thanks to all my reviewers, I love feedback. It's like food to my writing. Enjoy!

Disclaimer: Sorry, don't own anything.

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It was time for Chemistry, her first class with Logan and Rory was very happy. She hadn't had a chance to talk to him alone all day today and this was a class they had alone. She wanted to hear all about his trip to Fiji with his family. She knew he wasn't close to his family, his sister was no in college and she was the only family that he was honestly close with. She was so lost in her thoughts that she didn't realize she was about to run into someone until it was too late.

"Oof! I'm so sorry, I was completely spaced out there." Rory looked up and caught the sight of those familiar green eyes. Someone must be laughing somewhere at her dumb luck.

"We have to stop meeting like this. It's not good for your books." Landon laughed as he picked her books up off the ground for a second time that day. "You sure do like books, don't you?"

Rory raised her eyebrows at the boy. "Are you making fun of me?"

Landon smiled at her. "Maybe."

"Do you have a death wish? Books are amazing; everyone should read as much as I do." Rory glared at Landon, maybe not liking him wouldn't be too hard after all.

"Oh, you mean these things?" Landon asked as he showed her the books he had stashed away in his backpack.

Rory paled; maybe this would be harder than she thought. She really found a man that read extremely sexy. "Wow."

"Speechless twice in one day, is that normal for you? Or am I just that amazing?"

"Oh no, you're cocky too! I'm so sick of cocky boys, I have to look after three as it is. I don't need to add another to my list so if you'll excuse me." Maybe, again, that would be easier than she thought. Rory brushed past Landon on her way to find Logan; however, Landon wasn't finished.

"Well, Rory. Some people take that as teasing, which it was. You are a feisty one. Chilton should be very interesting. See you around." Landon winked at her, again, and found his way to his seat.

Rory blinked a few times, but she couldn't find the words. This day just wasn't turning out the way she thought it would go. She was now very confused about how she was supposed to feel about Landon. She didn't have much more time to think before Logan caught sight of her and was waving her over.

"Ace! Hey, I saved us some seats. They're even in the front of the classroom, just like you like it." Logan smiled, having seen her interaction with the new guy. He didn't know anything about this person and it made him a little uneasy. He made a mental note to have Finn dig around later. He had to found out more if he was showing this much interest in his Ace. _His_?

"Logan! I love you, you amazing socialite you!" Rory walked over to where Logan was seated and sat her stuff down at their workstation. "How are you? I feel like I haven't seen you all day. First we're separated for weeks then I don't even get to see you at school barely. Someone hates me!"

"Now Ace, no one could possibly hate you. I paid them to get away from you." Logan teased while he tugged at the ponytail Rory had thrown in her hair. It was the end of summer and still a little hot. Rory sometimes hated her long hair.

"So that's what it is. Well good, saved me money." Rory smiled at Logan and was about to say more when the teacher walked in.

"Good afternoon class. Welcome to Advanced Chemistry. Turn to the person setting next to you and meet your permanent lab partner. Now let's get started, shall we?"

Rory smiled. She had the whole semester to spend with Logan in Chemistry. She also had a new boy to learn all about. Life was truly interesting.

XXX

Fifth period was over and it was time to head to English, their final class of the day that all of them had together. Rory loved English, this just gave her another reason to love it.

"Now love, why don't you just give it up already? You know you can't resist the sexy Australian charm for forever." Finn was hitting on yet another girl. This time he was getting shot down. That seemed to be happening a lot lately. Rory laughed as she headed towards the back to sit with the girls. As a group, they usually sat towards the back even though Rory usually sat up front. She gave this up to be able to sit with her friends. She loved when they had classes together. This way, group projects were so much more fun and she wouldn't have to deal with Paris. It was a win-win situation.

"Hey guys. How were the rest of your classes?"

"Come on, Rory. Nobody likes school like you do. Classes were boring. If it weren't for all of the hot guys we would totally be a lost cause. I honestly don't know if I would even show up to school."

Leave it to Stephanie to not care. Rosemary at least kept up semi-decent grades. She was almost as equally boy obsessed though. "Lucky you have me to keep on you about your grades."

The girls rolled their eyes. "Yeah, lucky us."

XXX

School was finally over and Rory was back in front of her locker.

"Hey there, Ms. Gilmore-Hayden."

Rory turned around to see Landon smiling at her. She felt herself smile back. "Hey Landon, have a good first day at Chilton?"

"Yes, and I owe it all to you. It would be an even better day if you'd like to get a coffee with me and maybe we could get to know each other a little better."

"Thanks, but Ace here already has plans."

Logan surprised Rory, coming out of nowhere and placing his arms around her shoulders. "Hey Logan, what are you doing here?"

"Landon, was it? I'm terribly sorry but I haven't seen Rory in weeks and I've missed her. I need to catch up with my best friend. Maybe some other time."

Rory eyed Logan. He was right, but he didn't have to be so blunt about it. "Yeah, I'm sorry Landon. Maybe tomorrow?"

"Sure, that sounds good. See you around Rory." He turned and left her to Logan, his ego bruised slightly.

"Logan! Did you have to act like that? He's new and doesn't know anyone." Rory turned as Logan's arm slipped from her shoulder.

"I'm sorry Ace. I missed you and we know nothing about this new guy. Don't worry, I've got Finn on it." Logan smiled. He knew that would light a fire under her. He loved to see her get angry. It was cute.

"LOGAN ELIAS HUNTZBERGER! I am not your little sister. You three cannot keep treating me like one. Next year we're going to be at Yale and you can't keep this up! I won't let you." Rory slammed her locker door shut and headed outside.

Logan sighed; Rory sure reacted a little more than he thought she would. Maybe she was truly interested in this Landon guy. Logan didn't know why, but that worried him.

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Pleas review! I'll love you all forever! 


	4. No Apology Necessary

Hello everyone! I know I never update like I say I do and I'm truly sorry. But at least this time I have a semi-legitimate excuse. I got married last month! Anyways...I know this is an extremely short chapter but it's just a little filler/back story. It sets up the next chapter which will be a lot better, I promise! Enjoy!

XXXXXXX

Rory jumped into her car and sped off before Logan could stop her

Rory jumped into her car and sped off before Logan could stop her. The nerve of that guy, they never let her have any fun. It's always been that way since her sophomore year. Rory's eyes glazed over as she thought back to Tristan Dugrey. He was her first of many things: her first boyfriend, her first kiss, her first love. He was also the person who took her virginity. Things were going great, or so she thought, until that fateful day. Tristan called to say he was getting sent away to military school. Rory didn't understand. Since they started dating Tristan was the perfect teenager. He told her his dad was sending him away because he got caught breaking into Bowman's safe. Later, Rory found out the real reason. He cheated on Rory and knocked up the girl. They ran away in shame. Rory was broken for the rest of her sophomore year. The boys have been very overprotective ever since.

Rory was broken out of her daze as she pulled into Stars Hollow. The hardware sign that hung from Luke's caught her attention and her natural urge for coffee drew her towards it. She was very coffee deprived and didn't want to waste time parking at her house so she just parked on the street. She practically ran inside.

"Jess! I need coffee, now."

"What's the magic word?"

Rory looked at Jess. He was Luke's nephew and her newest friend. He just moved her this summer from New York. He was a rebel without a cause. She just saw someone who needed a friend. "Pretty please with a cherry on top?"

"Not it, but that'll do."

Rory sighed as she took the first sip after her long day at Chilton. She never appreciated coffee more than she did now.

"Fruit of my loins! Did you meet any hot new boy toys today in hell?!"

Rory looked up to see her mother run in with as much urgency for coffee as she did. "Mom you have no idea…." Rory laughed as she filled in her mother on her first day as Chilton's senior queen.

XXX

Rory walked into the halls of Chilton the next day. She had a mission. She had to find Landon and apologize for Logan the day before. Then, she had to find Logan and kick his ass. Rory spotted Landon as he was closing his locker.

"Hey Landon!"

"Good morning Gilmore. How's it going?"

Rory stared at Landon as he smiled down at her. She felt her insides turn to mush as her heart started to thump loudly in her chest. _Get it together Gilmore! _"Umm, I wanted to apologize for yesterday. Logan was entirely out of line and I'm sorry."

"Hey, no need to apologize. If I was best friends with someone as beautiful as you I would be overprotective too." Landon laughed at Rory's naivety. He definitely wouldn't like boys looking at her, especially new ones that nobody knew anything about.

"Well, he still shouldn't have been so rude. Can I make it up to you? I was thinking we could grab that cup of coffee today after school." Rory was hoping he would say yes. She really hates making a fool of herself…

"Sure. See you out in the courtyard after the last bell?"

"Yup." Rory smiled at him as he slung his backpack over his shoulder.

"See you later Rory." He leaned down and kissed her cheek. "Don't run into any one today. I'd hate for you to get hurt and miss our coffee date." He winked at her and headed down the hallway.

Rory just stared off at his retreating figure. She touched her cheek where his lips previously touched. She couldn't believe what was happening. Before she had time to move she saw Logan enter the school. He wasn't going to ruin her good mood so she stealthily sneaked by to her first class. Thank goodness she had taken that book home with her last night!

XXX

Little did Rory know that Logan had seen her and Landon's whole interaction. Something didn't sit well with him. He had to talk to Colin and Finn. They would know what to do.

So there it is. I am at a crossroads on my other story, Arranged Marriage. I'm not quite sure where I want to take it, but I will finish it. I swear! It would just make my day if you press that little button down there and let me know what you think. Until next time!


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